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I'm trying to design an Info Path form for a leave approval workflow.

Only a Head of Department can approve. The requirement is that if the applicants supervisor(manager) is not the Head of Department, route the workflow upwards to the supervisor(manager) of the supervisor(manager). This process would continue until a HOD is finally reached.

How do I create Info Path sections that repeat until an HOD is found

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So, in the final the HOD will receive the request for approval. Then why not using the people picker and select from the start the name of HOD and submit the form. I belive in every company the HOD is a known person. Then a workflow can get this info and send him an email to request an approval.

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Alternatively you could creaete a data source that pulls from the User Profile Service and loop through the varous levels of managers until it reaches the HOD.

You can create a data source for the UPS by creating a Soap Web Service that connects to: http://yoursite/vti_bin/UserProfileService.asmx?WSDL

Then you can create filter that passes the current user to the USP connection.

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